Datadog's Retention Analysis helps measure the long-term success of an application by tracking user engagement over time through high-level cohort graphs. This data enables developers to assess overall user satisfaction and identify pain points in their UX that can be optimized. By pivoting to other tools like Heatmaps and Session Replay, developers can troubleshoot these issues and create smoother user journeys. Retention Analysis also allows for the analysis of both user views and actions, as well as filtering based on various factors such as session type, browser, or country.